The landscape that we see around us today is the result of processes that have taken place at various timescales. There are cycles
of annual growth, cycles of perrenial growth, animal cycles, hydrological cycles, geological cycles and generational human disturbances that can be used to account for why the landscape is the way it is today. Those who are skilled at reading a landscape can tell an interesting story about why the current landscape has the form it has today and the forces that led to its present form. Most of us are not that good at reading the landscape as we don't spend enough time in nature in quiet contemplation of what the landscape is telling us about how it came to be that way. Books help, but there is no substitute for extended direct observation as Permaculture co-founder David Holmgren argues in this video (skip ahead to the 8:30 mark if you want to focus on his landscape reading thoughts):

The urban landscape has many forces operating over different timescales that determine its present form. Perhaps it would repay the effort to sit in quiet contemplation in front of a successful business and imagine all the forces that came together to make it successful. You can also be more interactive and ask the owners what factors have contributed to their success, although they alone cannot determine their fate - the forces within the larger landscape are major determining factors.

Books help in informing our observation as they might direct our observation towards aspects that we might be missing. A big influence on urban landscapes are the modes of transport that its residents typically use to get around. Do they typically walk, bike, take public transport, or drive to where they need to go? This can determine how traffic interacts with buildings and how cities are laid out. In the excellent textbook Urban Ecology: The Science of Cities (2014) Richard Forman
offers up this interesting but somewhat vague set of comparisons (p. 286):

Perhaps in a city where people walk and bike more often, successful buildings are more likely to be clumped together than in cities that mostly use motorized vehicles to get around? Factors like this may be
behind the patterning we see. Perhaps it would repay the effort to engage in direct observation of traffic patterns around locations to understand what type of transport passes in front of it, and interacts with it, and use that information in your design and thinking.

Some skills we can be acquired quickly, but as David points out some skills cannot be rushed and require extended periods of direct observation and interaction informed by past observations and current understandings. The ability to read the urban landscape is one of those skills. We all have the ability to some extent but it can be improved.